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New Yorkers trying for a road trip from Houston to New Orleans in October

we are attending a wedding in Houston in last week of October for 3 days. we can spare couple of more days for sight seeing. Searching around the city, didn't found anything interesting ( suggest if there is ), so we ( me my husband and a toddler) are planning to take a road trip to near by cities, here pops New Orleans.
I am clueless,as first time visiting southern part of country. Looking for suggestions for natural, scenic drives, places to eat around on the way to new Orleans or even near to Houston ( near woodlands area)? or there is better options go around Houston ?

I agree road trip possibilities are not very interesting in that area. If you decide to fly, consider places other than NOLA, and possibly wait until last minute to see what the weather will be before booking a flight.

I would not want to have to drive a rental car back to Houston after a trip to NOL.
FYI: The Amtrak Sunset Limited #2 leaves Houston at 12:10PM on Tuesday, Friday and Sunday arriving at 9:40PM (probably later).
This avoids a drop off charge and you can fly back from New Orleans.
I have actually eaten a fairly good Po'Boy sandwich on an Amtrak train on the way out of NOL.

Have you thought of going to Austin and/or San Antonio instead of New Orleans? The drive is not really any more scenic, but it's a shorter distance. (Houston - New Orleans is about 350 miles; Houston to San Antonio is 200 miles and Houston - Austin is about 170 miles.) There's lots to see and do in either of those cities and the Hill Country, even with a toddler in tow.

Where in Houston will you be staying? There are plenty of things to do in Houston with a toddler, and lots of great restaurants of all types and all price ranges. If you want to go on a road trip, I definitely would recommend Austin or San Antonio. Austin would be my first choice. It's an easy drive.